U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H13NO
Molecular Weight 151.206
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLPROPANOLAMINE

SMILES

C[C@@]([H])([C@@]([H])(c1ccccc1)O)N

InChI

InChIKey=DLNKOYKMWOXYQA-CBAPKCEASA-N
InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1

HIDE SMILES / InChI

Molecular Formula C9H13NO
Molecular Weight 151.206
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including http://www.druginfosys.com/drug.aspx?drugcode=569&type=1 | https://www.drugs.com/dosage/phenylpropanolamine.html | https://www.petcarerx.com/medication-guides/about-the-proin-dosage-for-urinary-incontinence/1086?page=all | https://www.federalregister.gov/documents/2014/02/20/2014-03596/phenylpropanolamine-withdrawal-of-approval-of-13-new-drug-applications-and-7-abbreviated-new-drug

(+)-Phenylpropanolamine is an enantiomer of propanolamine. The substance has low adrenergic activity and exerts measurable physiological effect only at high doses, which were lethal to experimental animals tested. Phenylpropanolamine belongs to the sympathomimetic amine class of drugs and is structurally related to ephedrine. The effects of phenylpropanolamine are largely the result of alpha-adrenergic agonist activity resulting from both direct stimulation of adrenergic receptors and release of neuronal norepinephrine. Phenylpropanolamine containing products has been withdrawn by FDA due to the association of phenylpropanolamine use with increased risk of hemorrhagic stroke.

Originator

Sources: C. Mannich and W. Jacobsohn, Ber., 43, 189 (1910).
Curator's Comment:: reference retrieved from http://www.sciencedirect.com/science/article/pii/S0099542808601719?via%3Dihub

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
PHENYLPROPANOLAMINE

Approved Use

Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Primary
PHENYLPROPANOLAMINE

Approved Use

Phenylpropanolamine (HCl) is mainly used as a nasal decongestant. Phenylpropanolamine (HCl) is also used as anorexiant in obesity
Primary
CODAMINE

Approved Use

Unknown

Launch Date

9.700992E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
107 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1104 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENYLPROPANOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Co-administed with::
brompheniramine, p.o(36 mg, single)
Sources: Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources: Page: p.825
Disc. AE: Cardiomyopathy...
AEs leading to
discontinuation/dose reduction:
Cardiomyopathy
Sources: Page: p.825
25 mg 2 times / day multiple, oral
Recommended
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources: Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources: Page: p.100
Disc. AE: Myocardial infarction...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction
Sources: Page: p.100
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: Page: p.52
Disc. AE: Vomiting, Hypertension...
AEs leading to
discontinuation/dose reduction:
Vomiting
Hypertension
Sources: Page: p.52
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
Disc. AE: Headache, Vomiting...
AEs leading to
discontinuation/dose reduction:
Headache (severe)
Vomiting
Intracranial hemorrhage
Sources: Page: p.510
AEs

AEs

AESignificanceDosePopulation
Cardiomyopathy Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Co-administed with::
brompheniramine, p.o(36 mg, single)
Sources: Page: p.825
healthy, 14
n = 1
Health Status: healthy
Age Group: 14
Sex: F
Population Size: 1
Sources: Page: p.825
Myocardial infarction Disc. AE
25 mg 2 times / day multiple, oral
Recommended
Dose: 25 mg, 2 times / day
Route: oral
Route: multiple
Dose: 25 mg, 2 times / day
Sources: Page: p.100
healthy, 25
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 25
Sex: F
Population Size: 1
Sources: Page: p.100
Hypertension Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: Page: p.52
Vomiting Disc. AE
2000 mg single, oral
Overdose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Co-administed with::
caffeine, p.o(8 g, single)
Sources: Page: p.52
unhealthy, 31
n = 1
Health Status: unhealthy
Condition: Schizophrenia
Age Group: 31
Sex: F
Population Size: 1
Sources: Page: p.52
Intracranial hemorrhage Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
Vomiting Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
Headache severe
Disc. AE
150 mg single, oral
Recommended
Dose: 150 mg
Route: oral
Route: single
Dose: 150 mg
Co-administed with::
caffeine, p.o(280 mg, single)
Sources: Page: p.510
healthy, 56
n = 1
Health Status: healthy
Condition: Weight control
Age Group: 56
Sex: F
Population Size: 1
Sources: Page: p.510
PubMed

PubMed

TitleDatePubMed
Intracranial hemorrhages due to phenylpropanolamine.
1985 May-Jun
Nifedipine therapy of phenylpropanolamine-induced hypertension.
1987 Feb
Phenylpropanolamine-induced psychosis. Potential predisposing factors.
1994 Sep
Dystonic reaction following recommended use of a cold syrup.
1995 Dec
Clarification--Drug risk in patients with glaucoma.
2001 Jun 11
Tolterodine once-daily: superior efficacy and tolerability in the treatment of the overactive bladder.
2001 Mar
Tolterodine: an overview.
2001 Nov
Pharmacological properties of A-204176, a novel and selective alpha1A adrenergic agonist, in in vitro and in vivo models of urethral function.
2001 Nov 30
Don't be so quick to ban medications.
2002 Jan 8
Implementation of the Comprehensive Methamphetamine Control Act of 1996; regulation of pseudoephedrine, phenylpropanolamine, and combination ephedrine drug products and reports of certain transactions to nonregulated persons. Final rule.
2002 Mar 28
Different responses to drugs against overactive bladder in detrusor muscle of pig, guinea pig and mouse.
2002 Nov 1
Excretion and detection of cathinone, cathine, and phenylpropanolamine in urine after kath chewing.
2002 Oct
A randomized controlled trial of tolterodine and oxybutynin on tolerability and clinical efficacy for treating Chinese women with an overactive bladder.
2002 Sep
Adrenergic drugs for urinary incontinence in adults.
2003
Both alpha1-adrenergic and D(1)-dopaminergic neurotransmissions are involved in phenylpropanolamine-mediated feeding suppression in mice.
2003 Aug 21
Simplified bladder training augments the effectiveness of tolterodine in patients with an overactive bladder.
2003 Jan
Use of Ephedra-containing products and risk for hemorrhagic stroke.
2003 Jan 14
Impact of a health education intervention in overactive bladder patients.
2004 Dec
Intramolecular chiral relay at stereogenic nitrogen. Synthesis and application of a new chiral auxiliary derived from (1R,2S)-norephedrine and acetone.
2004 Feb 6
Fatal pulmonary arterial hypertension associated with phenylpropanolamine exposure.
2004 Jul
A validated chiral HPLC method for the enantiomeric separation of tolterodine tartarate.
2004 Sep 3
Pharmacological management of overactive bladder : a systematic and critical review of published economic evaluations.
2005
[Therapy of bladder weakness].
2005 Jan 21
Economic impact of extended-release tolterodine versus immediate- and extended-release oxybutynin among commercially insured persons with overactive bladder.
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Validation of the urgency perception scale.
2005 Mar
Juvenile pig detrusor: effects of propiverine and three of its metabolites.
2005 Nov 7
Enantiomeric determination of ephedrines and norephedrines by chiral derivatization gas chromatography-mass spectrometry approaches.
2005 Oct 15
Nighttime dosing with tolterodine reduces overactive bladder-related nocturnal micturitions in patients with overactive bladder and nocturia.
2006 Apr
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.
2006 Dec
[Comment on the STAR study: Comparison of the efficacy and tolerance of solifenacin and tolterodine retard in the treatment of overactive bladder].
2006 Jul
Tolterodine extended release improves patient-reported outcomes in overactive bladder: results from the IMPACT trial.
2006 Jun
Tolterodine.
2006 Jun 6-12
Using anticholinergics to treat overactive bladder: the issue of treatment tolerability.
2006 Mar
Mass spectrometric data characteristics of commonly abused amphetamines with sequential derivatization at two active sites.
2006 Sep 12
Comparative evaluation of efficacy of use of tamsulosin and/or tolterodine for medical treatment of distal ureteral stones.
2007 Apr
Protracted 'pro-addictive' phenotype produced in mice by pre-adolescent phenylpropanolamine.
2007 Aug
Treatment of men with lower urinary tract symptoms and overactive bladder.
2007 Mar 21
Transcriptional interruption of cAMP response element binding protein modulates superoxide dismutase and neuropeptide Y-mediated feeding behavior in freely moving rats.
2008 May
Comparison of fesoterodine and tolterodine in patients with overactive bladder.
2008 Nov
Extended-release tolterodine with or without tamsulosin in men with lower urinary tract symptoms and overactive bladder: effects on urinary symptoms assessed by the International Prostate Symptom Score.
2008 Nov
How many drugs for LUTS due to BPH are too many?
2008 Sep
Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation.
2009 Jun 5
Ephedra alkaloids inhibit platelet aggregation.
2010 Apr
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Khat use and neurobehavioral functions: suggestions for future studies.
2010 Dec 1
Cystoscopic diagnosis and treatment of ectopic ureters in female dogs: 16 cases (2005-2008).
2010 Jul 15
Proof of principle: The effect of antimuscarinics on bladder filling sensations in healthy subjects--a placebo controlled double blind investigation using 4 and 8 mg tolterodine extended release.
2010 Mar
Syndrome of inappropriate antidiuretic hormone associated with tolterodine therapy.
2010 May
Targeting oxidative stress in the hypothalamus: the effect of transcription factor STAT3 knockdown on endogenous antioxidants-mediated appetite control.
2015 Jan
Patents

Sample Use Guides

Usual Adult Dose for Nasal Congestion 25 mg orally every 4 hours. -or- 75 mg orally extended release every 12 hours. Not to exceed 150 mg/day. Usual Adult Dose for Weight Loss 25 mg orally 3 times a day, one-half hour before meals. -or- 75 mg orally extended release once a day in the morning. The use of phenylpropanolamine for weight loss should be limited to 12 weeks.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: phenylpropanolamine inhibits platelet aggregation
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 14:11:39 UTC 2021
Edited
by admin
on Sat Jun 26 14:11:39 UTC 2021
Record UNII
33RU150WUN
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
PHENYLPROPANOLAMINE
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
PROPADRINE
Common Name English
RINEXIN
Brand Name English
NSC-9920
Code English
PHENYLPROPANOLAMINE [MI]
Common Name English
FANSIA
Brand Name English
BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, (R*,S*)-, (+/-)
Common Name English
NOREPHEDRINE
Common Name English
(+/-)-NOREPHEDRINE
Common Name English
PHENYLPROPANOLAMINE [HSDB]
Common Name English
PHENYLPROPANOLAMINE [MART.]
Common Name English
PHENYLPROPANOLAMINE [VANDF]
Common Name English
SELEGILINE HYDROCHLORIDE IMPURITY C [EP]
Common Name English
PHENYLPROPANOLAMINE [INN]
Common Name English
PHENYLPROPANOLAMINE [WHO-DD]
Common Name English
PHENYLFENESIN
Common Name English
Classification Tree Code System Code
WHO-ATC R01BA01
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
WHO-VATC QR01BA51
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
WHO-VATC QR01BA01
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
WHO-VATC QG04BX91
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
WHO-ATC R01BA51
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
NCI_THESAURUS C87053
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
CFR 21 CFR 1315.13
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
CFR 21 CFR 1314.20
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
CFR 21 CFR 520.1760
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL61006
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
EPA CompTox
14838-15-4
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
FDA UNII
33RU150WUN
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
MERCK INDEX
M8687
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
PHENYLPROPANOLAMINE
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
NCI_THESAURUS
C29364
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
DRUG CENTRAL
2149
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
INN
4955
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
CAS
14838-15-4
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
RXCUI
8175
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY RxNorm
EVMPD
SUB09790MIG
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
HSDB
6485
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
DRUG BANK
DB00397
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
238-900-2
Created by admin on Sat Jun 26 14:11:41 UTC 2021 , Edited by admin on Sat Jun 26 14:11:41 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> INHIBITOR
SUB_CONCEPT->SUBSTANCE
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC